Sai's Challenge
by YawnyPenguin
Summary: Sai is set a new challenge by Naruto to prove he is not homosexual. Challenge: Get three phone numbers before midnight!
1. The Bet

**DISCLAIMER: I DO NOT OWN NARUTO**

Sai's Challenge

The Bet

Today was the Festival of Konoha and everyone was dressed in traditional Japanese clothing like kimonos. Lanterns lit up the streets and stalls were set up with food and games. Naruto and Sakura walked down the street together (Sakura wearing a female kimono and Naruto wearing a male one of course) when they saw Sai. In a kimono. For girls.

"Hey! Sai! What's up with the full female kimono?!" Naruto shouted with a laugh from across the street as they walked over to him.

"I read that for festivals you wear traditional clothing." Sai replied.

"Yeah but that's for girls Sai!" Sakura added.

"It was the only one the shop had... Then should I take it off?"

"Are you wearing anything underneath..?" Naruto asked unsure then once Sai took it off, he was wearing his normal ninja outfit, "I've always been wondering what was up with you showing your stomach..."

"It obviously gives more flexibility Naruto!" Sakura said.

"In a book, it said that girls like people who show their abs..."

"You don't even like girls Sai," Naruto said.

"Yeah, now you come to mention it... Sai's never really been interested has he? Well, apart from the time he called Ino gorgeous..."

"You make me sound like a homosexual,"

"You might be Sai... You might be..."

"I'm not Naruto! Really!"

"Assuming you were, it would explain a lot... Like time with the grave robbers! You kept smiling at me then you made a move on me and you said you were 'showing me some tenderness' so I ran off. It all makes sense!"

"It wasn't like that Naruto! The book said that when a friend is scared or frightened about something, gently place your hand around their shoulder. Let them know their not alone and show them some tenderness."

"I wasn't scared! If anything, I was scared of you. Smiling at me all weird and creepy..."

"What about the time when you kissed Sasuke?"

"That was an accident! And who told you that anyway? You want to prove you're not homosexual, then I bet you you can't get three phone numbers by midnight. If you do, then I'll take back everything I said and I'll never mention it ever again,"

"Ok. I will."

"Also, you're not allowed to get any phone numbers from Sakura, Hinata, Ino or Tenten and don't cheat by getting any phone numbers from any guys either! You can start...now!"

Sai's new mission had began.

**Get three girls phone numbers before midnight!**


	2. The First Girl

The First Girl

"Hello, may I have your phone number?" Sai asked to a random girl he saw.

"No." she replied quickly as she walked away.

_Hm, I wonder what I did wrong... Maybe I'll try that girl over there. Oh, no. She's walking away... I'll just follow her._ Sai thought to himself. He started to follow her and after a few minutes the girl quickened her speed seeing Sai creepily smiling at her as he followed. Finally he caught up with her.

"Hello, I've been following you for a while," Sai said to the girl, "May I have-"

"AHH! GO AWAY YOU PERVERTED STALKER!" she screamed as she landed a big punch on Sai's left cheek like Sakura would with Naruto then she ran away scared leaving Sai grasping his cheek in pain as people look at him all weird on the street.

"W-Wait!"

_This might be harder than I thought. I don't see what I did wrong... Maybe I should just go get a book._ Sai thought to himself in the middle of the crowded street. He made his way to the library and looked for a good book.

"Understanding A Girls Feelings... Make-Out Tactics... How Girls Work. This might be good. Girls appreciate it when you compliment them. Picking features of their appearance is a good way of starting conversation like talking about her eyes. " he began reading quietly, "Ok, this seems simple enough."

He made his way down the street once again and found his next target.

"Hello, your eyes are ugly," he said.

"If you don't have anything nice to say, just fuck off." she said with a face like thunder. He quickly walked away and found someone else to hit on.

He slowly approached her and said, "Hello, your eyes are dark brown," whilst smiling and looking adorably awkward.

"Hm, yes, yes they are..." she said smiling back.

_Sakura didn't like me calling her ugly. Ino liked me calling her gorgeous. The girl before didn't like being called ugly. So girls like it when you say they are attractive..._ Thought Sai.

"You're beautiful," Sai said.

"Why thank you... What's your name? I'm Akari,"

"My name's Sai,"

"Nice to meet you Sai! What's with the um, cheek thing?"

"I-I got punched,"

"Oh. Does it hurt..?"

"Um-hm. May I have your number please?" he said nervous.

"Hm... Yeah, sure, why not," she said whilst quickly using a pen and a small piece of paper from a stall to write down her number, "Here," she said as she gave it to him.

"Thank you," Sai said.

"Well, I'd gotta go... Call me, bye!" Akari said before walking away from Sai.

_That wasn't hard... Because I'm not gay. Am I? No. Now I've got to do that two other times._ Sai thought to himself.

**It was on. He was sure Naruto would lose the bet.**

* * *

~ Sorry... I have failed you... This wasn't a good chapter I know... ~

**HAPPY NEW YEAR EVERYONE!**


	3. The Second Girl

The Second Girl

_I have three hours left to get another two phone numbers..._

"Hello, you're beautiful," Sai said to another girl.

"I just saw you get another girls number you tool," she said back.

"Oh, no, you see-"

"Just leave it." she said as she walked away.

_Maybe I should target girls in a different crowd_. Sai thought to himself. He walked along the street to the opposite side and saw Naruto walking with Sakura, Ino, Shikamaru and Choji.

"Oh, hey Sai. So how's it goin'?" Naruto asked.

"I've already got one number," Sai answered.

"Oh. We heard someone scream something about a stalker a while ago. Let's see you work your magic on the next lucky girl then!" Naruto said whilst the others smiled close to laughing.

"Ok. Hello little one, you're beautiful," he said to a little girl whilst the rest of them were speechless.

"Paedophile alert(!)" Naruto whispered to the others.

"M-Mommy!" she shrieked.

"Oh, are you alright? **YOU TWISTED PAEDOPHILE!**" her mother accused angry.

"Gosh Sai, you're sick!" Ino shouted.

**"OK SAI YOU PIECE OF CRAP! IS THIS A JOKE?! YOUR SICK IN THE HEAD! YOU DON'T HIT ON A LITTLE GIRL!"** shouted Sakura furious with her right hand clenched in a fist ready to beat the shit out of him, **"CHAA!"** she punched him high into the sky as everyone stared and Sai wailed in pain. Sakura forced a smile and laughed awkwardly and nervously in front of everyone and she said, "Hehe... Sorry to disturb you! Hehe..."

A mile away by the gates, Sai was in a pain with a seriously bruised left cheek beginning to swell and he thought to himself: _Sakura's never punched me so hard... I've never seen Naruto punched so hard either... So I'm not allowed to try get numbers from little girls... I have around two hours and forty-five minutes left._

He got up after five minutes of laying there and he began to walk remembering the challenge Naruto set him.

He chose his next victim and said, "Hello, you're beautiful,"

"Oh gosh, are you ok?"

"Yes. Are you?"

"No, like, the left side of your face is red and purple. It hurts doesn't it?"

"It hurts..."

"You should get yourself checked,"

"No, it's fine,"

"No, I'll take you. Come on,"

_The book said girls would usually take pity on you when you are injured or alone. I knew it._

After ten minutes they arrived.

"Ok, you can go from here. I gotta go."

"W-Wait. Can I get your number please?"

"Yeah, ok, here. I hope we meet again sometime!"

"Um-hm," Sai said with a small wave as she walked away. He was taken to a room and healed by a basic medical nin then was forced to wait thirty minutes before being released.

**_Now, I've got one and a half hours left before midnight. I just need one number._**


	4. Midnight

Midnight

_Even when they treated me it still hurts a little... But I can still win this bet. It's just one more number._

"Hey! You should check out the tavern! The ladies are all over you!" a drunk man said sleazily to another as Sai overheard.

_Hmm, the tavern. A tavern is where people get drunk. If the women are drunk they might be easier to get numbers from._

Five minutes later, he arrived at the tavern and entered being greeted by a rowdy crowd of people. He sat in a booth and soon three women approached him.

"A cutie like you shouldn't have to sit alone. Mind if we join you?" one asked. They didn't wait for an answer and sat down beside him.

"What brings you here?"

"I-" Sai started when some other women came over.

"HEY! You didn't tell us there was another young one!" one said as she sat down.

"So, what are you doing here?"

"I-I'm here to get a phone number..."

"You can have my number!" a women said as they wrote it quickly on a tissue as another one said, "Here!"

_I should have come here a while ago. This is easy._

The women basically threw themselves at him and he did not know what to do.

"I'm going to go." he said as he stood up.

"What? No! Stay!"

"No I-" he started but was dragged back down viciously.

"It's not even midnight yet!"

_These women... They scare me... I have... six... seven. Seven numbers but now I need to get to Naruto before midnight..._

"No, I really need to-"

Sai kept trying to make a break for it but was always dragged back down and the women (now around ten of them) were completely unaware they were harassing him and he seriously could not escape.

Forty-five minutes later when Sai couldn't handle any more of it, Sai really forced himself out of the horde of women and ran desperately to the door clutching it in his hands in case the women would try to pull him back. He swung the door and ran like hell down the street.

"Come back soon!" a woman shouted from the door smiling eagerly.

_I need to get to Naruto before it's too late. I won't be able to find him in ten minutes if I go by foot._

He took out his scroll and brush and quickly drew a bird then said, "Ninja Art: Super Beast Scroll," then he used his bird to find Naruto quicker.

"There he is. Naruto! Naruto!" Sai shouted to Naruto surrounded by Sakura, Ino, Choji and Shikamaru. He flew down and landed presenting Naruto with all seven numbers he collected, "I got all three of them and an extra four Naruto!"

"So the paedophile got seven numbers," Shikamaru said.

"So he won the bet. Good for him," Choji added.

"What?! S-So you did get all three numbers? And more?" Naruto said with a slightly embarrassed tone of voice.

"So Naruto you lose," Sakura said, "You didn't even get more numbers than Sai!"

"Get more numbers than me?"

"Yep! After Naruto made the bet with you, he wanted to see how many numbers he could get also. In the end, he got-"

"No! Don't say it!" Naruto shouted.

"Two!"

"So I got more than Naruto?"

"Um-hm,"

"I win the bet and win with the women too,"

"Fine, I guess you're not gay..."

**"Yes, I'm not gay!" Sai said happy.**

* * *

~ The End ~

~ Sorry, this was a pretty bad ending but I didn't have anymore ideas and I didn't want to leave you guys hanging so I finished it up... Sorry! But I hope you enjoyed it anyway! Thank you for reading! ~

~ YawnyPenguin ~


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